Triethylamine → 4-(1,1-Dioxido-2-isothiazolidinyl)phenylboronic Acid Pinacol Ester

HRID 425946Notes

Reaction equation

[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.C(N(CC)CC)C.Cl[CH2:25][CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl.CCOC(C)=O.O>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:15]=[CH:14][C:12]([N:13]3[CH2:25][CH2:26][CH2:27][S:28]3(=[O:30])=[O:29])=[CH:11][CH:10]=2)[O:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5 g, 22.8 mmol) was dissolved in DCM (100 mL, 0.2M), triethylamine (15 mL, 5.0 molar equivalent) was added to the mixture. The reaction was stirred at 0° C. for 5 min. 3-chloropropane-1-sulfonyl chloride (4.2 g, 23.0 mmol) was added portion wise. The reaction was stirred at 0° C. for 1 hr and brought gradually to room temperature, heated to reflux at 70° C. for 2 hr. The mixture was cooled to room temperature, diluted with EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified through a silica column to afford 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]isothiazolidine 1,1-dioxide as off-white solid (5.2 g, 70% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.62 (d, 2H), 7.18 (d, 2H), 3.76 (t, 2H), 3.53 (t, 2H), 2.41 (t, 2H), 1.28 (s, 12H).

Workup

stirringThe reaction was stirred at 0° C. for 1 hr
custombrought gradually to room temperature
temperatureheated
temperatureto reflux at 70° C. for 2 hr
temperatureThe mixture was cooled to room temperature
washThe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified through a silica column

Sources & evidence

ORD record: ord-6817c9d906554191995552b9b277373b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106197B2

Reaction notes

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